2-(1-Benzylpiperidin-4-ylamino)-5-methylpyridine → 5-Methyl-N-(piperidin-4-YL)pyridin-2-amine

HRID 2223875Notes

Reaction equation

HRID 2223875 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 230211122-(1-Benzylpiperidin-4-ylamino)-5-methylpyridine

Product 1

HCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amineYield 77.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 2-(1-benzylpiperidin-4-ylamino)-5-methylpyridine (11.3 g) in ethanol (250 mL) was added 20% palladium hydroxide (4 g). After stirring the solution at room temperature under hydrogen atmosphere for 48 hours, 20% palladium hydroxide (2 g) was further added. The solution was then stirred at room temperature under hydrogen atmosphere for additional 99 hours. The catalyst was filtered off. After concentration under reduced pressure, the resulting residue was purified by chromatography [NH silica gel, chloroform:methanol=10:1]. The resulting crude product was crystallized from ethyl acetate/hexane to give the title compound (5.97 g).

Workup

  1. stirringThe solution was then stirred at room temperature under hydrogen atmosphere for additional 99 hours
  2. filtrationThe catalyst was filtered off
  3. concentrationAfter concentration under reduced pressure
  4. customthe resulting residue was purified by chromatography [NH silica gel, chloroform:methanol=10:1]
  5. customThe resulting crude product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-600fdf2fbc314cac98efbbf722e6cbd1
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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